Literature DB >> 10768188

Facile synthesis of O6-alkyl-, O6-aryl-, and diaminopurine nucleosides from 2'-deoxyguanosine

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Abstract

The 3',5'-bis-O-TBDMS derivative of 2'-deoxyguanosine can be converted to its O6-alkyl and O6-aryl ethers as well as to N6-substituted diaminopurine nucleosides in two simple steps. Also described is a novel, nonaqueous, one-step O6-desulfonylation method that leads to deprotection of the carbonyl moiety of 2'-deoxyguanosine.

Entities:  

Year:  2000        PMID： 10768188     DOI： 10.1021/ol005564m

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  7 in total

1.  Independent Generation and Reactivity of 2'-Deoxyguanosin-N1-yl Radical.

Authors:  Liwei Zheng; Marc M Greenberg
Journal:  J Org Chem       Date:  2020-06-11       Impact factor: 4.354

2.  Independent Photochemical Generation and Reactivity of Nitrogen-Centered Purine Nucleoside Radicals from Hydrazines.

Authors:  Liwei Zheng; Lu Lin; Ke Qu; Amitava Adhikary; Michael D Sevilla; Marc M Greenberg
Journal:  Org Lett       Date:  2017-11-10       Impact factor: 6.005

3.  Two-step, one-pot synthesis of inosine, guanosine, and 2'-deoxyguanosine O6-ethers via intermediate O6-(benzotriazol-1-yl) derivatives.

Authors:  Hari Prasad Kokatla; Mahesh K Lakshman
Journal:  Curr Protoc Nucleic Acid Chem       Date:  2012-06

4.  A simple method for C-6 modification of guanine nucleosides.

Authors:  Mahesh K Lakshman; Josh Frank
Journal:  Org Biomol Chem       Date:  2009-06-01       Impact factor: 3.876

5.  C-C cross-coupling reactions of O6-alkyl-2-haloinosine derivatives and a one-pot cross-coupling/O6-deprotection procedure.

Authors:  Venkateshwarlu Gurram; Narender Pottabathini; Ramesh Garlapati; Avinash B Chaudhary; Balaram Patro; Mahesh K Lakshman
Journal:  Chem Asian J       Date:  2012-05-08

6.  Novel synthesis of O6-alkylguanine containing oligodeoxyribonucleotides as substrates for the human DNA repair protein, O6-methylguanine DNA methyltransferase (MGMT).

Authors:  Takayuki Shibata; Nicola Glynn; T Brian H McMurry; R Stanley McElhinney; Geoffrey P Margison; David M Williams
Journal:  Nucleic Acids Res       Date:  2006-04-11       Impact factor: 16.971

7.  1,2,3-Triazoles as leaving groups: SNAr reactions of 2,6-bistriazolylpurines with O- and C-nucleophiles.

Authors:  Dace Cīrule; Irina Novosjolova; Ērika Bizdēna; Māris Turks
Journal:  Beilstein J Org Chem       Date:  2021-02-11       Impact factor: 2.883
  7 in total

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